This just occurred to me as a possibly better way to select start points than the current "toward the back corner of the bed" method I've been using.
Create an edge selection interface where the user can select polygon edges in the model. Any loop that intersects with a selected edge uses that edge vertex as the starting point for that loop. The user might select overlapping edges resulting in multiple intersections on a given loop. To handle that, allow drag and drop of the edges to prioritize which gets used first.
Thoughts?